AR041182A1 - Derivados de fenoxipropenilfenilo y su uso como herbicidas - Google Patents
Derivados de fenoxipropenilfenilo y su uso como herbicidasInfo
- Publication number
- AR041182A1 AR041182A1 ARP030102332A AR041182A1 AR 041182 A1 AR041182 A1 AR 041182A1 AR P030102332 A ARP030102332 A AR P030102332A AR 041182 A1 AR041182 A1 AR 041182A1
- Authority
- AR
- Argentina
- Prior art keywords
- alkyl
- substituted
- halogen
- twice
- once
- Prior art date
Links
- 239000004009 herbicide Substances 0.000 title 1
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 abstract 31
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 28
- 229910052736 halogen Inorganic materials 0.000 abstract 28
- 150000002367 halogens Chemical class 0.000 abstract 28
- 229910052739 hydrogen Inorganic materials 0.000 abstract 28
- 239000001257 hydrogen Substances 0.000 abstract 28
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 23
- 125000003342 alkenyl group Chemical group 0.000 abstract 19
- 125000000304 alkynyl group Chemical group 0.000 abstract 19
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 abstract 18
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 18
- 150000002431 hydrogen Chemical class 0.000 abstract 17
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 16
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 16
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 14
- 125000000217 alkyl group Chemical group 0.000 abstract 13
- 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 abstract 10
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 abstract 10
- 125000004414 alkyl thio group Chemical group 0.000 abstract 9
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 abstract 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 7
- 125000002947 alkylene group Chemical group 0.000 abstract 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 5
- 229910052717 sulfur Chemical group 0.000 abstract 5
- -1 C1- alkoxy 4 Chemical group 0.000 abstract 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 4
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 3
- 125000005842 heteroatom Chemical group 0.000 abstract 3
- 229910052757 nitrogen Inorganic materials 0.000 abstract 3
- 229910052760 oxygen Inorganic materials 0.000 abstract 3
- 239000001301 oxygen Substances 0.000 abstract 3
- 239000011593 sulfur Chemical group 0.000 abstract 3
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 abstract 2
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 abstract 2
- 125000006619 (C1-C6) dialkylamino group Chemical group 0.000 abstract 2
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 abstract 2
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 125000004644 alkyl sulfinyl group Chemical group 0.000 abstract 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 abstract 2
- 125000000262 haloalkenyl group Chemical group 0.000 abstract 2
- 125000004430 oxygen atom Chemical group O* 0.000 abstract 2
- 125000006413 ring segment Chemical group 0.000 abstract 2
- 125000004434 sulfur atom Chemical group 0.000 abstract 2
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 abstract 1
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 abstract 1
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 abstract 1
- 125000003341 7 membered heterocyclic group Chemical group 0.000 abstract 1
- 101100275375 Arabidopsis thaliana COR47 gene Proteins 0.000 abstract 1
- 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract 1
- 229920006395 saturated elastomer Polymers 0.000 abstract 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/54—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and etherified hydroxy groups bound to the carbon skeleton
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/36—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
- A01N37/38—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/27—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups
- C07C205/34—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups bound to carbon atoms of six-membered aromatic rings and etherified hydroxy groups bound to acyclic carbon atoms of the carbon skeleton
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/27—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups
- C07C205/35—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C205/36—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton to carbon atoms of the same non-condensed six-membered aromatic ring or to carbon atoms of six-membered aromatic rings being part of the same condensed ring system
- C07C205/38—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton to carbon atoms of the same non-condensed six-membered aromatic ring or to carbon atoms of six-membered aromatic rings being part of the same condensed ring system the oxygen atom of at least one of the etherified hydroxy groups being further bound to a carbon atom of a six-membered aromatic ring, e.g. nitrodiphenyl ethers
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
- C07C205/56—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups bound to carbon atoms of six-membered aromatic rings and carboxyl groups bound to acyclic carbon atoms of the carbon skeleton
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/76—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings and etherified hydroxy groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/78—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
- C07C217/80—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings
- C07C217/82—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring
- C07C217/84—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring the oxygen atom of at least one of the etherified hydroxy groups being further bound to an acyclic carbon atom
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- C—CHEMISTRY; METALLURGY
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C225/00—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones
- C07C225/02—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to acyclic carbon atoms of the carbon skeleton
- C07C225/04—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being saturated
- C07C225/08—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being saturated and containing rings
- C07C225/10—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being saturated and containing rings with doubly-bound oxygen atoms bound to carbon atoms not being part of rings
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- C—CHEMISTRY; METALLURGY
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/16—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
- C07C233/24—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring
- C07C233/25—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
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- C—CHEMISTRY; METALLURGY
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/42—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/44—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
- C07C235/46—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/32—Oximes
- C07C251/34—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
- C07C251/48—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with the carbon atom of at least one of the oxyimino groups bound to a carbon atom of a six-membered aromatic ring
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- C—CHEMISTRY; METALLURGY
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
- C07C255/32—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring
- C07C255/37—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by etherified hydroxy groups
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
- C07C39/18—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring monocyclic with unsaturation outside the aromatic ring
- C07C39/19—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring monocyclic with unsaturation outside the aromatic ring containing carbon-to-carbon double bonds but no carbon-to-carbon triple bonds
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- C07C39/24—Halogenated derivatives
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- C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
- C07C39/24—Halogenated derivatives
- C07C39/26—Halogenated derivatives monocyclic monohydroxylic containing halogen bound to ring carbon atoms
- C07C39/27—Halogenated derivatives monocyclic monohydroxylic containing halogen bound to ring carbon atoms all halogen atoms being bound to ring carbon atoms
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- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/23—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing hydroxy or O-metal groups
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- C—CHEMISTRY; METALLURGY
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/52—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings
- C07C47/575—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings containing ether groups, groups, groups, or groups
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- C—CHEMISTRY; METALLURGY
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
- C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
- C07C59/66—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings
- C07C59/68—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings the oxygen atom of the ether group being bound to a non-condensed six-membered aromatic ring
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- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/74—Unsaturated compounds containing —CHO groups
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- C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C65/21—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing ether groups, groups, groups, or groups
- C07C65/28—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing ether groups, groups, groups, or groups having unsaturation outside the aromatic rings
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- C07C67/00—Preparation of carboxylic acid esters
- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
- C07C67/31—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by introduction of functional groups containing oxygen only in singly bound form
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- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
- C07C69/84—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring
- C07C69/92—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring with etherified hydroxyl groups
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- Chemical & Material Sciences (AREA)
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- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
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- General Health & Medical Sciences (AREA)
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Abstract
Reivindicación 1: Compuestos de la fórmula (1) en la cual R01 representa hidrógeno, alquilo C1-8, alquenilo C3-8 o alquinilo C3-8; o R01 representa fenilo o fenil-alquilo C1-6, pudiendo por su parte los anillos fenilo estar substituidos de una a cinco veces con halógeno, y/o una, dos o tres veces con alquilo C1-4, halo-alquilo C1-4, alcoxi C1-4, -CN, -NO2, alquiltio C1-8, alquilsulfinilo C1-8 o alquilsulfonilo C1-8; o R01 representa alquilo C1-8 substituido de una a cinco veces con halógeno o substituido una, dos o tres veces con -CN, alquilamino C1-6, di(alquil C1-6)amino o alcoxi C1-4; n representa 0, 1, 2, 3 o 4; cada uno de los R1 independientemente de los demás, representa halógeno, -CN, -SCN, -SF5, -NO2, -NH2, -CO2R7, -CONR8R9, -C(S)NH2, -C(R10)=NOR11, -COR12, -OR13, -SR14, -SOR15, -SO2R16, -OSO2R17, alquilo C1-8, alquenilo C2-8, alquinilo C2-8 o cicloalquilo C3-6; o representa alquilo C1-8, alquenilo C2-8 o alquinilo C2-8 substituidos de una a cinco veces con halógeno o substituidos una, dos o tres veces con -CN, -NO2, -NR18R19, -CO2R20, -CONR21R22, -COR23, -C(R24)=NOR25, -C(S)NR26R27, -C(alquiltio C1-4)=NR28, -OR29, -SR30, -SOR31, -SO2R32 o cicloalquilo C3-6; y/o cada uno de los R1 independientemente de los demás, representa cicloalquilo C3-6 substituido de una a cinco veces con halógeno o substituido una, dos o tres veces con -CN, -NO2, -NR18R19, -CO2R20, -CONR21R22, -COR23, -C(R24)=NOR25, -C(S)NR26R27, -C(alquiltio C1-4)=NR28, -SR30, -SOR31, -SO2R32 o cicloalquilo C3-6; y/o cada uno de los R1 independientemente de los demás, representa fenilo, que por su parte puede estar substituido de una a cinco veces halógeno o una, dos o tres veces con alquilo C1-4, haloalquilo C1-4, alcoxi C1-4, -CN, -NO2, alquiltio C1-4, alquilsulfinilo C1-4 o alquilsulfonilo C1-4; y/o dos R1 adyacentes juntos forman un puente alquileno C1-7, que puede estar interrumpido por 1 a 3 heteroátomos seleccionados entre oxígeno, nitrógeno y azufre y que puede estar substituido de una a cinco veces con halógeno y/o una, dos o tres veces con alquilo C1-6 o alcoxi C1-6, siendo la cantidad total de átomos de anillo por lo menos de 5 y a lo sumo de 9; y/o dos R1 adyacentes juntos forman un puente alquenileno C2-7, que puede estar interrumpido por 1 a 3 heteroátomos seleccionados entre oxígeno, nitrógeno y azufre y que puede estar substituido de una a cinco veces con halógeno y/o una, dos o tres veces con alquilo C1-6 o alcoxi C1-6, siendo la cantidad total de átomos de anillo por lo menos de 5 y a lo sumo de 9; R3 y R4 independientemente entre sí, representan hidrógeno, halógeno, -CN, alquilo C1-4 o alcoxi C1-4; o R3 y R4 juntos forman alquileno C2-5; R7 representa hidrógeno, alquilo C1-8, alquenilo C3-8 o alquinilo C3-8, o alquilo C1-8, alquenilo C3-8 o alquinilo C3-8 substituidos de una a cinco veces con halógeno, y/o una, dos o tres veces con alcoxi C1-4 o fenilo, pudiendo fenilo a su vez estar substituido de una a cinco veces con halógeno, y/o una, dos o tres veces con alquilo C1-6, haloalquilo C1-4, alcoxi C1-6, -CN, -NO2, alquiltio C1-6, alquilsulfinilo C1-4 o alquilsulfonilo C1-4; R8 representa hidrógeno o alquilo C1-8; R9 representa hidrógeno o alquilo C1-8, o es alquilo C1-8 substituido una, dos o tres veces con -COOH, alcoxicarbonilo C1-8 o -CN, o R9 representa alquenilo C3-8, alquinilo C3-8, fenilo o bencilo, pudiendo fenilo y bencilo por su parte estar substituidos de una a cinco veces con halógeno y/o una, dos o tres veces con alquilo C1-4, haloalquilo C1-4, alcoxi C1-4, -CN, -NO2, alquiltio C1-4, alquilsulfinilo C1-4 o alquilsulfonilo C1-4; o R8 y R9 conjuntamente representan alquileno C2-5; R10 representa hidrógeno, alquilo C1-4, haloalquilo C1-4 o cicloalquilo C3-6; R11 representa hidrógeno, alquilo C1-8, alquenilo C3-8, alquinilo C3-8, haloalquilo C1-4, o haloalquenilo C3-6; R12 representa hidrógeno, alquilo C1-4, haloalquilo C1-4 o cicloalquilo C3-6; R13 representa hidrógeno, alquilo C1-8, alquenilo C3-8 o alquinilo C3-8; o R13 representa fenilo o fenil-alquilo C1-6, pudiendo por su parte los anillos fenilo, estar substituidos de una a cinco veces con halógeno y/o una, dos o tres veces con alquilo C1-4, halo-alquilo C1-4, alcoxi C1-4, -CN, -NO2, alquiltio C1-8, alquilsulfinilo C1-8 o alquilsulfonilo C1-8, o R13 representa alquilo C1-8 substituido de una a cinco veces con halógeno o una, dos o tres veces con -CN, alquilamino C1-6, di(alquil C1-6)amino o alcoxi C1-4; R14 representa hidrógeno, alquilo C1-8, alquenilo C3-8 o alquinilo C3-8, o alquilo C1-8 substituido de una a cinco veces con halógeno o una, dos o tres veces con -CN o alcoxi C1-4; R15, R16 y R17 independientemente entre sí, representan alquilo C1-8, alquenilo C3-8 o alquinilo C3-8, o alquilo C1-8 substituido de una a cinco veces con halógeno, o substituido una, dos o tres veces con -CN o alcoxi C1-4; R18 representa hidrógeno o alquilo C1-8; R19 representa hidrógeno, alquilo C1-8, alquenilo C3-8, alquinilo C3-8, fenilo o bencilo, pudiendo fenilo y bencilo por su parte estar substituidos de una a cinco veces con halógeno o estar substituidos una, dos o tres veces con alquilo C1-4, haloalquilo C1-4, alcoxi C1-4, -CN, -NO2, alquiltio C1-4, alquilsulfinilo C1-4 o alquilsulfonilo C1-4; o R18 y R19 representan conjuntamente una cadena alquileno C2-5, que puede estar interrumpida por un átomo de oxígeno o por un átomo de azufre; R20 representa hidrógeno, alquilo C1-8, alquenilo C3-8, alquinilo C3-8, fenilo o bencilo, pudiendo fenilo y bencilo por su parte estar substituidos de una a cinco veces con halógeno y/o substituido una, dos o tres veces con alquilo C1-4, haloalquilo C1-4, alcoxi C1-4, -CN, -NO2, alquiltio C1-4, alquilsulfinilo C1-4 o alquilsulfonilo C1-4; R2 representa hidrógeno o alquilo C1-8; R22 representa hidrógeno o alquilo C1-8, o alquilo C1-8 substituido una, dos o tres veces con -COOH, alcoxicarbonilo C1-8 o -CN, o R22 representa alquenilo C3-8, alquinilo C3-8, fenilo o bencilo, pudiendo fenilo y bencilo por su parte estar substituidos de una a cinco veces con halógeno y/o una, dos o tres veces con alquilo C1-4, haloalquilo C1-4, alcoxi C1-4, -CN, -NO2, alquiltio C1-4, alquilsulfinilo C1-4 o alquilsulfonilo C1-4; o R21 y R22 conjuntamente representan alquileno C2-5; R23 representa hidrógeno, alquilo C1-4, haloalquilo C1-4 o cicloalquilo C3-6; R24 representa hidrógeno, alquilo C1-4, haloalquilo C1-4 o cicloalquilo C3-6; R25 representa hidrógeno, alquilo C1-8, alquenilo C3-8, alquinilo C3-8, haloalquilo C1-4 o haloalquenilo C3-6; R26 representa hidrógeno o alquilo C1-8; R27 representa hidrógeno o alquilo C1-8, o alquilo C1-8 substituido una, dos o tres veces con -COOH, alcoxicarbonilo C1-8 o -CN, o R27 representa alquenilo C3-8, alquinilo C3-8, fenilo o bencilo, pudiendo fenilo y bencilo por su parte estar substituidos de una a cinco veces con halógeno y/o substituidos una, dos o tres veces con alquilo C1-4, haloalquilo C1-4, alcoxi C1-4, -CN, -NO2, alquiltio C1-4, alquilsulfinilo C1-4 o alquilsulfonilo C1-4; o R26 y R27 conjuntamente representan alquileno C2-5; R28 representa hidrógeno o alquilo C1-8; R29 y R30 independientemente entre sí, representan hidrógeno, alquilo C1-8, alquenilo C3-8 o alquinilo, o alquilo C1-8 substituido de una a cinco veces con halógeno, o substituidos una, dos o tres veces con -CN o alcoxi C1-4; R31 y R32 independientemente entre sí, representan alquilo C1-8, alquenilo C3-8 o alquinilo C3-8, o alquilo C1-8 substituido de una a cinco veces con halógeno, o una, dos o tres veces con -CN o alcoxi C1-4; m vale 1, 2, 3, 4 o 5; cada uno de los R2 independientemente de los demás, representa halógeno, -CN, -SCN, -OCN, -N3, -SF5, -NO2, -NR33R34, -CO2R35, -CONR36R37, -C(R38)=NOR39, -COR40, -OR41, -SR42, -SOR43, -SO2R44, -OSO2R45, -N([CO]pR46)COR47, -N(OR54)COR55, -N(R56)SO2R57, -N(SO2R58)SO2R59, -N=C(OR60)R61, -CR62(OR63)OR64, -OC(O)NR65R66, -SC(O)NR67R68, -OC(S)NR69R70 o -N-ftalimida; y/o R2 representa un sistema de anillo heterocíclico de 5 a 7 miembros que puede ser aromático, parcial o totalmente saturado y que puede contener de 1 a 4 heteroátomos seleccionados entre nitrógeno, oxígeno y azufre, pudiendo dicho sistema de anillo heterocíclico a su vez estar substituido de una a cinco veces con halógeno y/o una, dos o tres veces con alquilo C1-4, haloalquilo C1-4, hidroxi-alquilo C1-4, alcoxi C1-4, haloalcoxi C1-4, alcoxi C1-4-alquilo C1-4, -CN, -NO2, alquiltio C1-6, alquilsulfinilo C1-6 o alquilsulfonilo C1-6; R33 representa hidrógeno o alquilo C1-8; y R34 representa hidrógeno, alquilo C1-8, alquenilo C3-8, alquinilo C3-8, fenilo o bencilo, pudiendo fenilo y bencilo a su vez estar substituidos de una a cinco veces con halógeno, y/o una, dos o tres veces con alquilo C1-4, haloalquilo C1-4, alcoxi C1-4, -CN, -NO2, alquiltio C1-4, alquilsulfinilo C1-4 o alquilsulfonilo C1-4; o R33 y R34 conjuntamente representan una cadena alquileno C2-5, que puede estar interrumpida por un átomo de oxígeno o por un átomo de azufre; R35 representa hidrógeno, alquilo C1-8, alquenilo C3-8 o alquinilo C3-8, o alquilo C1-8, alquenilo C3-8 o alquinilo C3-8 substituidos de una a cinco veces con halógeno o una, dos o tres veces con alcoxi C1-4 o fenilo, pudiendo fenilo por su parte estar substituido de una a cinco veces con halógeno y/o una, dos o tres veces con alquilo C1-4, haloalquilo C1-4, alcoxi C1-4, -CN, -NO2, alquiltio C1-4, alquilsulfinilo C1-4 o alquilsulfonilo C1-4; R36 representa hidrógeno o alquilo C1-8; R37 representa hidrógeno o alquilo C1-8, o representa alquilo C1-8 substituido una, dos o tres veces con -COOH, alcoxicarbonilo C1-8 o -CN, o R37 representa alquenilo C3-8, alquinilo C3-8, fenilo o bencilo, pudiendo fenilo y bencilo a su vez estar substituidos de una a cinco veces con halógeno y/o una, dos o tres veces con alquilo C1-4, haloalquilo C1-4, alcoxi C1-4, -CN, -NO2, alquiltio C1-4, alquilsulfinilo C1-4 o alquilsulfonilo C1-4; o R36 y R37 juntos representan alquileno C3-5; R38 representa hidrógeno, alquilo C1-4, haloalquilo C1-4 o cic
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| US8097712B2 (en) | 2007-11-07 | 2012-01-17 | Beelogics Inc. | Compositions for conferring tolerance to viral disease in social insects, and the use thereof |
| US8962584B2 (en) | 2009-10-14 | 2015-02-24 | Yissum Research Development Company Of The Hebrew University Of Jerusalem, Ltd. | Compositions for controlling Varroa mites in bees |
| US9121022B2 (en) | 2010-03-08 | 2015-09-01 | Monsanto Technology Llc | Method for controlling herbicide-resistant plants |
| CA2848689A1 (en) | 2011-09-13 | 2013-03-21 | Monsanto Technology Llc | Methods and compositions for weed control targeting pds |
| MX350775B (es) | 2011-09-13 | 2017-09-15 | Monsanto Technology Llc | Métodos y composiciones para el control de malezas. |
| CN103957697B (zh) | 2011-09-13 | 2017-10-24 | 孟山都技术公司 | 用于杂草控制的方法和组合物 |
| CA2848576A1 (en) | 2011-09-13 | 2013-03-21 | Monsanto Technology Llc | Methods and compositions for weed control comprising topical application of 4-hydroxyphenyl-pyruvate-dioxygenase (hppd)-inhibiting polynucleotides |
| EP3434779A1 (en) | 2011-09-13 | 2019-01-30 | Monsanto Technology LLC | Methods and compositions for weed control |
| UA116090C2 (uk) | 2011-09-13 | 2018-02-12 | Монсанто Текнолоджи Ллс | Спосіб та композиція для боротьби з бур'янами (варіанти) |
| WO2013040116A1 (en) | 2011-09-13 | 2013-03-21 | Monsanto Technology Llc | Methods and compositions for weed control |
| US10829828B2 (en) | 2011-09-13 | 2020-11-10 | Monsanto Technology Llc | Methods and compositions for weed control |
| US10806146B2 (en) | 2011-09-13 | 2020-10-20 | Monsanto Technology Llc | Methods and compositions for weed control |
| US10760086B2 (en) | 2011-09-13 | 2020-09-01 | Monsanto Technology Llc | Methods and compositions for weed control |
| US10240162B2 (en) | 2012-05-24 | 2019-03-26 | A.B. Seeds Ltd. | Compositions and methods for silencing gene expression |
| US10683505B2 (en) | 2013-01-01 | 2020-06-16 | Monsanto Technology Llc | Methods of introducing dsRNA to plant seeds for modulating gene expression |
| BR112015015975A2 (pt) | 2013-01-01 | 2018-11-06 | A. B. Seeds Ltd. | moléculas de dsrna isoladas e métodos de uso das mesmas para silenciamento das moléculas alvo de interesse. |
| UA121846C2 (uk) | 2013-03-13 | 2020-08-10 | Монсанто Текнолоджи Ллс | Спосіб та гербіцидна композиція для контролю видів рослини роду lolium |
| UA123082C2 (uk) | 2013-03-13 | 2021-02-17 | Монсанто Текнолоджи Ллс | Спосіб та гербіцидна композиція для боротьби з видами рослин роду sorghum |
| US10568328B2 (en) | 2013-03-15 | 2020-02-25 | Monsanto Technology Llc | Methods and compositions for weed control |
| CN105980567B (zh) | 2013-07-19 | 2021-04-16 | 孟山都技术有限公司 | 用于控制叶甲属的组合物和方法 |
| US9850496B2 (en) | 2013-07-19 | 2017-12-26 | Monsanto Technology Llc | Compositions and methods for controlling Leptinotarsa |
| ES3008698T3 (en) | 2013-11-04 | 2025-03-24 | Greenlight Biosciences Inc | Compositions and methods for controlling arthropod parasite and pest infestations |
| UA119253C2 (uk) | 2013-12-10 | 2019-05-27 | Біолоджикс, Інк. | Спосіб боротьби із вірусом у кліща varroa та у бджіл |
| UA121462C2 (uk) | 2014-01-15 | 2020-06-10 | Монсанто Текнолоджі Елелсі | Спосіб та композиція для боротьби із бур'янами з використанням полінуклеотидів epsps |
| EP3420809A1 (en) | 2014-04-01 | 2019-01-02 | Monsanto Technology LLC | Compositions and methods for controlling insect pests |
| EP3158067B1 (en) | 2014-06-23 | 2020-08-12 | Monsanto Technology LLC | Compositions and methods for regulating gene expression via rna interference |
| WO2015200539A1 (en) | 2014-06-25 | 2015-12-30 | Monsanto Technology Llc | Methods and compositions for delivering nucleic acids to plant cells and regulating gene expression |
| US10378012B2 (en) | 2014-07-29 | 2019-08-13 | Monsanto Technology Llc | Compositions and methods for controlling insect pests |
| WO2016118762A1 (en) | 2015-01-22 | 2016-07-28 | Monsanto Technology Llc | Compositions and methods for controlling leptinotarsa |
| WO2016196738A1 (en) | 2015-06-02 | 2016-12-08 | Monsanto Technology Llc | Compositions and methods for delivery of a polynucleotide into a plant |
| EP3302030A4 (en) | 2015-06-03 | 2019-04-24 | Monsanto Technology LLC | METHOD AND COMPOSITIONS FOR INTRODUCING NUCLEIC ACIDS IN PLANTS |
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